Flights to Chicago overview
Going searches for the best fares and sends members deals bookable 1-12 months in advance. Going members save approximately 39% compared to normal flight prices to Chicago.
Cheapest Going deal
Average price roundtrip
Average Going deal price roundtrip
Best month to fly
Going found the most deals with travel dates in October.
Worst month to fly
Going found the least deals with travel dates in June.
Top tips for finding a cheap flight to Chicago
Book in the Goldilocks Window
There is no perfect calculation for the exact date you should book a flight. However, there is a range. We call it the Goldilocks Window because it’s not too far away from your departure date, but not too close either; it’s that sweet spot when you’re most likely to find a great deal. This just-right time is 1–3 months before a domestic flight and 2–8 months before an international flight.
If you plan to travel during peak season or your dates aren’t flexible, start looking even earlier. This means if you hope to take a vacation during the December holiday season, it’s smart to start looking for flights in July.
We know it’s tempting to hold out for a last minute deal, but those deals are very rare. In fact, fare jumps happen 21, 14, and 7 days ahead of travel dates, so it’s best to book before those points.
Use the Greek Islands Trick
The Greek Islands Trick is one of our beloved tips for getting to expensive islands during peak travel seasons, but it works for Chicago, too. Basically, you get as close as you can to your final destination, then find another short flight or an alternate travel mode for your last leg.
So, if flights to Chicago in July are crazy expensive, look for flights to Indianapolis; Milwaukee; Madison, Wisconsin; or Grand Rapids, Michigan. From there, you can take the train, bus, or rent a car. It takes more time but could save you a few hundred bucks.
Search alternative departure airports
Travelers living near, say, Houston who are looking to fly to Chicago may never have considered flying out of another airport. Why would you when you have such a large airport right there? Believe it or not, there may be situations when you could save money by flying out of another airport. We see deals from airports all over the country, so it’s worth looking around. If there’s another airport within driving distance, like Austin or New Orleans, compare prices to Houston before booking.
If you’re traveling from outside of the US, it could even be worth flying to an alternative airport. If you live in Athens, for example, look for flights from Dublin or London to Chicago. If you see a great deal, it could be worth taking a budget airline flight to one of those cities before heading across the ocean.
Fly when it’s cheaper
Summer is by far the busiest travel season in Chicago. If you can, look for flights during shoulder seasons, like April and May or September and October, when the weather isn’t too cold and there are fewer crowds and cheaper prices. And if you can stand the cold, you’ll likely find some amazing flight and hotel deals in January and February.
If you plan to travel during the summer, at least try to look for fares on what are generally the cheapest days to fly: Tuesdays, Wednesdays, and Saturdays. Avoid Fridays and Sundays, the most expensive days to fly, if you can.
Set alerts for specific trips
Flight alerts are your friend. They will help save time searching for flights and help you avoid frustration when you miss a deal. Simply set a flight alert for the dates you hope to travel (or multiple dates if you’re flexible), and wait for an alert telling you prices have dropped. It’s best to do this well before your trip so you can see prices drop during the Goldilocks Window we talked about.
O’Hare is one of the world’s busiest airports, serving more than 30 million passengers per year and with direct flights from more than 240 cities around the world. It’s a hub for both United and American, plus serves numerous international airlines, along with Delta and Southwest flights. Add on Midway, with another 8.8 million passengers and lots of Southwest and low-fare carriers, and your odds of finding a decent flight to Chicago are pretty high.
Frequently asked questions about flying to Chicago
When is high season in Chicago?
Summer is Chicago’s busiest season. It’s when neighborhood festivals abound, it’s warm enough to take advantage of the numerous Lake Michigan beaches and city parks, and patios pop up at seemingly every restaurant. While June–August is busy in general, Lollapalooza week––usually in late July or early August—can be especially crowded. Chicago is a large city that plays host to major concerts, sporting events, broadway shows, and festivals, so check the calendar before booking.
When is the best time to visit Chicago?
Summer in Chicago is busy for a reason. It’s also one of the best times to visit and when the city’s outdoor activities really shine. May and September–October are also great months. The weather should still be nice enough to spend some time outdoors, and in the fall you’ll see the leaves changing colors. Plus, you’ll avoid most of the crowds.
Chicago can be extremely cold from December–March, and February is probably the most brutal month. That also means it’s the least popular time to visit, yet a great time to find affordable flights and hotel rooms. There’s plenty to do indoors in Chicago, from museums to world-class restaurants, comedy, and theater. If you don’t mind a little chill, come visit and feel like a local braving the negative wind chill.
How many airports are there in Chicago?
There are two airports in Chicago: O’Hare International Airport (ORD) and Chicago Midway International Airport (MDW). O’Hare is on the northwest side of the city, and Midway is on the southwest side. O’Hare is much busier and the airport most people will fly into.
Which airport is the closest to Chicago?
Midway is about 12 miles from downtown, while O’Hare is 18 miles. Depending on traffic, a taxi or Uber from Midway will be about $10-15 cheaper than from O’Hare. Both are connected to the Loop—Chicago’s downtown area—via the “L,” the city’s metro system. Both also have taxi stands and rideshare pickup areas.
How long is the flight to Chicago?
If you’re flying from around the US, most flights to Chicago will be 2–3 hours. From California, it will be 4–5 hours, and from Miami it will be closer to 4. If you’re visiting from outside the US, flight times depend on where you’re coming from. Nonstop flights from Europe are around 8–10 hours. From Mexico City, flights are just 4 hours. Elsewhere, they can range from 8–20 hours, but you can usually reach Chicago with just one stop.
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* Prices are per person and include all taxes & fees in USD. All prices were accurate at the time of publishing, however, prices are not guaranteed, as airline pricing can change by the minute. Average Going fares are based on average prices of deals found by Going.